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Unexpected structural defects in a main-chain conjugated polymer synthesized through Suzuki-Miyaura cross coupling polymerization

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Title: Unexpected structural defects in a main-chain conjugated polymer synthesized through Suzuki-Miyaura cross coupling polymerization
Authors: Yuan, Yuehui Browse this author
Song, Zhiyi Browse this author →KAKEN DB
Bando, Masayoshi Browse this author
Nakano, Tamaki Browse this author →KAKEN DB
Keywords: The Suzuki reaction
Side reactions
Alternating copolymer
Issue Date: 4-Jun-2021
Publisher: Elsevier
Journal Title: Polymer
Volume: 226
Start Page: 123769
Publisher DOI: 10.1016/j.polymer.2021.123769
Abstract: Suzuki-Miyaura cross coupling (SMC) copolymerization of 3,8-dibromo-1,10-phenanthroline (PhenBr(2)) and 9,9-dioctylfluorene-2,7-diboronic acid (DOF[B(OH)(2)](2) was conducted aiming to synthesized an alternating copolymer composed of 1,10-phenanthroline-3,8-diyl and 9,9-dioctylfluorene-2,7-diyl units in a mixture of 1,2-dimethoxyethane and water using Pd(PPh3)(4) and K2CO3 as catalysts at different temperatures. Side reactions were unexpectedly found to take place in the reactions at 100 degrees C where hydroxy and carbonyl groups appeared to be introduced probably to 1,10-phenanthroline units. Such reactions were more remarkable in the polymerization than in a model reaction leading to a triad molecule consisting of central 1,10-phenanthroline-3,8-diyl unit connected to two 9,9-dioctylfluorene-2-yl units, suggesting that a longer growing species has a role in such reactions. The extent of side reactions was higher with H2O than with D2O and was negligible with (H2O)-O-18. The polymer with structural defects showed photo absorbance and emission profiles and thermal properties which were remarkably different from those of the alternating copolymer without structural defects.
Rights: © 2021. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
http://creativecommons.org/licenses/by-nc-nd/4.0/
Type: article (author version)
URI: http://hdl.handle.net/2115/89626
Appears in Collections:触媒科学研究所 (Institute for Catalysis) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 中野 環

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